


Matchmaker Papyrus and his Two Tsunderes

by ReadWithDetermination



Series: When Two Tsunderes Go on A Date, Does the Void Implode? [2]
Category: Undertale (Video Game)
Genre: Alternate Universe - Fellswap, Comedy, Comedy of Errors, Dating, F/M, Fellswap - Freeform, Fellswap Papyrus - Freeform, Fellswap Sans is Secretly a Vanilla Bean, First Dates, First Kiss, Fluff and Humor, Genderless Roommate Character, Humor, Language of Flowers, M/M, Matchmaking, Mild Language, Papyrus Just Wants His Bro to Be Happy, Podfic & Podficced Works, Podfic Available, Podfic Length: 30-45 Minutes, Pranks and Practical Jokes, References to Addiction, References to Depression, References to Drugs, Showing Off, Suicidal Thoughts, The Author Regrets Nothing, Tsundere Sans (Undertale), Undertale Monsters on the Surface, Wooing, fellswap sans - Freeform, genderless reader
Language: English
Status: Completed
Published: 2019-12-01
Updated: 2020-01-23
Packaged: 2021-02-26 05:40:06
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,490
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21628510
Author URL: https://archiveofourown.org/users/ReadWithDetermination/pseuds/ReadWithDetermination
Summary: Addition to "To My Date, With Hate, Love Sans":(FellSwap Surface AU)Papyrus wanted to repay you for being a supportive friend while he kicked some bad habits, and he loves his bro and wants him to be happy.  When he finds out that both you and his brother are completely oblivious to your mutual crushes, he schemes with your roommate in order to remedy that.  A comedy of errors ensues because you're both tsundere as hell and Papyrus doesn't have enough BBQ sauce for that.
Relationships: Sans/Reader, papyrus & oc
Series: When Two Tsunderes Go on A Date, Does the Void Implode? [2]
Series URL: https://archiveofourown.org/series/1558828
Comments: 23
Kudos: 89





	1. Chapter 1

**Author's Note:**

  * For [Brishton](https://archiveofourown.org/users/Brishton/gifts).
  * Inspired by [To My Date, With Hate, Love Sans](https://archiveofourown.org/works/21607558) by [ReadWithDetermination](https://archiveofourown.org/users/ReadWithDetermination/pseuds/ReadWithDetermination). 



> I had a lovely reader comment on "To My Date, With Hate, Love Sans" about wanting to see more, so even though I initially had only planned a oneshot, my fingers did the clicky-clacky on the keyboard and I wound up with this little gem. 
> 
> Fellswap is probably the hardest Undertale Au to peg down in terms of fanon "canon". Because of this, I went with Sans having red magic, Sans being cruel to Papyrus as a way to survive Underground but it still deeply affecting Papyrus, and Papyrus having been both a smoker an drug user as a way to cope with life Underground (obviously, there are minor trigger warnings related to references of depression, past drug abuse, past suicidal thoughts, etc. so be warned).
> 
> However, the fic only starts out angsty due to background knowledge, and gets funnier. It's a sort of precursor and retelling of TMDWHLS from an outsider's perspective. 
> 
> Enjoy!

Papyrus had to admit: life on the Surface was far better than he had ever dared to dream.

Sure, the transition had not been without its hardships. 

It had taken a few months for everything to smooth over with the local human population. But monster gold was worth its weight in...well, GOLD, and the technological advances made by monsters during their time beneath the Surface was enough to win over most of their governments. Then there was the fact that magic could serve a great many purposes. No longer were monsters forced to forever remain vigilant, unable to tap into much of anything besides their most powerful offensive magics. Now their healers stepped forth, exuding green magic as a way to help combat human diseases. Humans were in awe by them.

Papyrus let out a harsh bark of a laugh. Humans leaders once lusted for their power and made their followers fear monsters when they could not harness magic themselves. Now, their greed for what the monsters provided was the very reason they were allowed back onto the Surface without a drop of blood being shed.

As a monster, he was granted a certain status simply by existing, and most humans seemed to be far more forgiving of monsters than their own kind. Papyrus realized that this was in part by how exotic monsters appeared to be - at least, for a while. Over time, the hype had died down, but he still got stares and some humans went out of their way to accommodate others like him.

Of course, there were a handful of people who still feared them or wanted to use monster magic for their own gain, but thugs of that sort never faired well. None of them had ever lived in the Underground, where the only rule was kill or be killed, and it showed.

Papyrus' main challenge came in the form of kicking certain habits he developed Underground.

You see, all monsters had their way of coping with the dangers of living before they were freed. You did what you had to stay sane - or, in the very least, not think about how each day, each minute, each second ticked by to another one identical to it, with no hope in sight of it ever changing. Papyrus knew many monsters that had freely given themselves up as free LV simply because they couldn't take the misery of it all, and how many more had he known to fall down after allowing despair to creep in?

Monsters did what they had to not to think about the endless cycle of run, fight, hide, wait.

Everyone had their vices.

You just had to make sure you did not become the vice.

Papyrus' main vice was cigarettes. He may not have had lungs, but he was still able to glean some reaction from the nicotine in them. The same went for his lesser used-but-even-unhealthier crack habit. 

It was harder for monsters to get addicted to substances than humans, simply due to their genetic makeup, and even more so for skeleton monsters, but Papyrus wouldn't lie...it took every fucking ounce of willpower he had not to give into his depression and just leap off into the Abyss just so he wouldn't have to continue enduring it all anymore. It was so damn hard to have to do the same thing over and over again each day. He hated always having to watch his back when he just wanted to rest. He hated his brother's biting insults. He hated knowing that any day could be the last day he ever saw his brother. All it would have taken was one lucky hit with enough hatred and-

The skeleton shook his head.

Things were so much different now.

Up here, Papyrus could finally close his eyes for more than a few moments out in the open without the worry of someone trying to dust him.

Standing there with his face turned toward the sun, allowing the strong ultraviolet light to bleach his bones, he felt cleansed. It was as if the very warmth of that great flaming ball in the sky was searing out all of the rotten and horrible parts of his past, leaving him warm and toasty as he basked in its glory.

To him, the sun meant acceptance - acceptance of his past and relief that he could finally, FINALLY look forward to a bright future.

It was the kid who was behind his going to rehab.

The kid hadn't had the best life, either. Both of their parents had been strung out on drugs when the child had set off on their own, hoping to find a better life for themselves than the rancid smell of a crack house. Losing their child even for that brief time turned out to be exactly what they needed to be scared straight, and they had entered a program in a desperate attempt to turn their lives around to be there for the kid they way they should have been to start.

After their temporary guardian had showed him pictures of the sort of squalor the kid had lived in, it was like a sock to the gut. The kid faced down so much shit for all of them, so the least he could do was kick the habit the way their parents were trying to.

After seeing the progress the kid's parent's made, he checked himself into the same program. He had a few ups and downs, as it was difficult to find a trained monster who hadn't gone batshit insane from living Underground to help with monster clients, but he managed alright. His normally laidback nature and punny comebacks actually made him fairly popular with some of the staff and clients there. This included a certain nurse.

Upon his graduating from the program (though, did anyone ever graduate something that was a lifelong process?), the nurse put him in touch with a good therapist to help him work through more of his issues.

They also put him in touch with you once they saw how well he was doing.

Papyrus really liked you. 

You were stubborn as hell, he'd give you that, but you were good at being able to supply a verbal kick in the pants whenever he was getting too down on himself. You were confidant, clever, encouraging, snarky, and always willing to drag him out of the house or just sit on the couch and watch reruns with him until his blues went away. You'd already helped support one friend through their recovery, so you had an innate gift for discerning when he needed a laugh and when he just needed a day to unwind and get it all out. The nurse was right - you were just the sort of friend he needed right now.

He just wished there was some way to repay you.

Oh, he had tried. He'd tried giving you gold, but you only accepted just enough for gas money now and then when he tagged along, or perhaps a free meal or two (you loved Mexican food). He tried to put in a good word with some of the other monsters he knew - ones that had adapted well to Surface life and had become successful in their own right. You had refused that, too. Papyrus had asked everyone from the kid to the nurse to even his brother, but no one seemed to have any idea how he could pay you back.

Until one day when he was over visiting your roommate, and you came screeching into the house with a confession he wasn't meant to hear but made him drop his BBQ sauce, nevertheless.

You had a crush on his brother!

Papyrus wanted to give you a hug and twirl you around the room for that one. In fact, he did just that, but you didn't actually know his motivation behind it

It was such a huge relief that the person his brother had been over the moon for had also taken a shine to him in return.

Sans had been forced to be a hardass for so long that it had actually been harder for him to tone down his behaviors than it was for Papyrus to kick his bad habits. The smaller skeleton had always had to be tough for the both of them. Few monsters dared mess with Sans when he supplanted himself as the Captain of the Royal Guard, Snowdin Division, and they knew better than to mess with Papyrus by association (not that Papyrus couldn't handle himself - after all, who do you think trained with Sans growing up?). But with the almost tyrannical exterior came Sans' only way to cover how much he cared about his brother: treating him so badly in front of everyone else that they wondered if he treated his own brother that badly when he screwed up, then what would he do to people he had no connection to whatsoever?

Papyrus knew he couldn't completely excuse the bullying and Sans had gone overboard at times, but he knew his brother had good intentions. The smaller skeleton was still shit with his emotions, but at least he tried. Once he found out just how much harm his insults had caused Papyrus, Sans set out immediately to try to rectify all of his past grievances. Gone were the demands to call Sans this-or-that title or to do demeaning acts, like announce why he even liked puns was a sign of his own mental default. Now, Sans actually encouraged his brother to speak up, to tell him what he wanted to eat or what new place to explore. Instead of being tugged after his brother with a leash attached to his collar, Sans now fell into step behind him, watching over him with the caution of an alpha wolf.

The behaviors felt smothering at times, but Papyrus appreciated the gesture.

So seeing Sans actually not know what to do with himself over a crush brought Papyrus greater joy than all the puns he could ever devise.

The problem with growing up Underground and having to play the part of a badass officer of the Royal Guard was that Sans had a great deal of emotional constipation. He just did not know how to react around you! Oh, sure, he could go on and on about how you did this, or how you did that, and why did you do this for so-and-so without reason? 

(That soon became a thinly-veiled 'why did they do this for so-and-so and not me?')

It wasn't until after Sans stood up in the middle of another usually peaceful dinner and announced that he was going to date you if it was the last thing he ever did that Papyrus realized how deep his brother was into you.

He tried to help. Really, Papyrus did. The truth of the matter is that, in a world of kill or be killed, it was hard to trust somebody long enough to get to know them very - and forget dating anyone. Alliances were tedious things to maintain. So without any experience of his own, Papyrus really couldn't give Sans any personal pointers. 

He DID dig up an old book Sans had found at the dump years ago about humans' courting etiquette. Sans had kept it on the offhand chance that "learning to seduce a human would bring them right to his clutches". Of course, Sans had barely been older than him at the time and Papyrus was fairly certain he had no idea what the word "seduce" even meant back then, but Papyrus knew why he really kept the book. He hid it well nowadays, but Sans had always held a fondness for certain parts of the rare human movies and books they were able to come across. Papyrus had to laugh now when he recalled stumbling upon one of Sans' secret reads and what he found on the page bookmarked.

The spine had literally nearly been worn away by how many times it was obvious Sans had flipped to it.

His poor, sweet vanilla bean of an older brother had nearly worn a book out because of a scene where the hero and heroine just _brushed hands_.

There was probably something to be said for that. Not having much positive physical contact and being touch-staved and whatnot because few wanted to risk dying over a tryst Underground. At least, not unless you were powerful enough that you felt you didn't have to worry about being taken out while your guard was down.

The problem with Sans is he took everything to an extreme in attempts to hide his feelings for you but also to try to win you over. 

And he was so, so bad at it!

Whenever you showed up to watch one of his sparring matches with Alphys, Sans couldn't help but try to show off how strong he was. Alphys, always willing to show off to her scientist girlfriend, was more than willing to go all out to show off her own skills - something that made the fish monster darting around out of the way of wayward attacks on the sidelines absolutely swoon.

You never swooned, and more than often spat a bunch of swears at Sans for nearly taking your head off with a misplaced bone attack, but you had admitted to Papyrus that you were highly impressed.

Papyrus had to talk Sans down from trying to up his game by leveling Mt. Ebott from the outside after he learned about that.

Neither was Sans very good at compliments.

Papyrus, having been on the receiving end of some of Sans' actual cruelty before, knew there wasn't a mote of actual spite in anything he said to you. He was quick to cover up his compliments by masking them with a taunt or an insult that even Papyrus wanted to facepalm over, but you, being the innocent person you were, seemed to take the bait every time as if Sans had been serious.

He had to admit - Sans was a brilliant tactician, and getting you riled up enough that you were willing to go literally head-to-head with him in challenges to spend time with you was genius. And don't think Papyrus missed the way Sans' eyelights would light up whenever you would playfully take a sock at him. He'd joked around that Sans should just ask you for a hug, but the one time you actually tackled him after your favorite sports team had won, Sans started hissing and spitting like a cat and Papyrus couldn't get him out of the closet for an _hour_.

(You had been extremely careful the next week not to touch him for fear of upsetting him or possibly sending him in an anxiety attack like you knew some trauma survivors had to deal with. Sans had moped the entire week. Papyrus hadn't felt such blissful peace in his house since monsters were freed until the day he convinced you that it wasn't your touch that had upset Sans, but his just being caught off guard. You took the "wounded pride" excuse, hook, line and sinker, and Sans went back to his maniacal plotting to skirt around his feelings some more.)

There were times Sans had managed to do well with you. The moment your roommate mentioned you had caught the flu, Sans had demanded he be allowed to see you and immediately headed straight to your place. Your roommate had chuckled as they messaged you work had gone late (it hadn't) so they were sending a friend to watch over you. Papyrus and the nurse had spent the rest of the evening snacking on BBQ nachos and marathoning an anime Alphys had loaned Sans as the text messages from both parties trickled through:

The panic of his brother worrying you were about to "fall down". 

Your angry confusion as to why Sans was there. 

Sans panicking over what temperature to make tea so "the damn human would drink it". 

Your shock over Sans making you tea - and, for some reason, asking what cyanide tasted like.

To be honest, the messages were funnier than anything on the television, and the anime was soon forgotten in favor of the real drama unfolding.

Sans had hoped his showy displays would send you running into his arms, but to be frank? You were just as bad as he was with your feelings.

How two people could dance around one another, only coming in to take playful nips like a pair of love-drunk beta fish were beyond him!

It was as if fate had deemed it necessary to take the densest monster in all of creation and put them together with the densest human on the planet and say, "Okay! Now kiss!"

It was painful to watch.

Hilarious, but painful.

It frustrated your roommate to no end, too, so Papyrus had crafted a clever alliance with them in order to try to get you and his brother to see what was right in front of your faces. But all of his quips and your roommates hints have fallen upon deaf ears. For heaven's sake, even that barista at the coffee shop besides your work had tried to give you suggestions! 

You two were practically already an item, and every damn person on the planet could see it - except you and Sans!

He was almost tempted to join your roommate in locking you both in the closet until you duked it out (or made out, he didn't really care) when the perfect opportunity presented itself:

Sans challenged you to a date.

"Brother, you're the only monster I know that would _challenge_ someone to a date," Papyrus had reiterated after Sans had dragged him from your house. 

Sans had promptly told him to shut up and help him find something to look presentable. As tempting as it was, Papyrus actually helped him pick out a decent outfit for the evening to help wow you instead of trolling him by trying to trick him into wearing a joke suit covered in cartoon ducks (you may have tried to hide that rubber duck you'd doodled the red eyes onto, but your roommate was a little shit and sold you out the moment your secret was out in the open).

Not surprisingly, Sans put a lot of effort into impressing you without making it look like he was trying to. If anything, it looked exactly the opposite - like he was trying to get a rise out of you like usual. At that point, Papyrus wasn't sure how much of Sans' behaviors was pulling your proverbial pigtails and how much of it was because he enjoyed riling you up. He supposed it was a bit of both.

He wanted to play by your rules, and somehow fit his heart in amongst the pieces. 

Sans had taken your words to heart about "glitzy" dates - all except for the suit, of course, because he wanted to make a good impression. Instead of taking you to a fancy restaurant, he chose Taco Loco, which was your favorite fast food joint. The bouquet may have been made from flowers he scooped up from the roadside, but he put a surprising amount of effort into choosing ones to convey what he was truly feeling without giving himself away entirely. He took to it as a new puzzle and wondered aloud to papyrus if you would figure it out.

Daisies to hope you would figure out the meaning. Goldenrod to hope you would accept his feelings and to encourage you to act upon romantic reciprocation. Finally, a single white clover head in the center of it all - a seemingly odd choice, but one whose meaning made perfect sense: "think only of me".

Papyrus was quite proud of how sappy his brother still was, deep down. Even with as far as he came, seeing the small remnants of an innocent young monster poking out from beneath his harsh exterior.

He also found your challenges incredibly amusing, so there was no way he was missing out on this one.

Both Papyrus and your roommate had front row seats to travesty.

He was so glad he had ordered you a copy of the dating guide he gave Sans. 

When the two of them showed up to gather you and your friend for the "date", it was all he could do to hold it together and not start laughing. It seemed either you had taken the book's advice to heart or had just anticipated Sans' first move, because you showed up to the door in an outfit that, save for a few accents, was entirely in the shade of Sans' magic. Sans' eyelights had actually blinked out for a moment. The act might have been taken as him realizing you were starting with your more powerful attacks, but not to Papyrus.

No, Papyrus could practically FEEL the soulbeat that pulsed the moment Sans saw you wearing...THAT.

"One point for Sans, and one point for you," your roommate said, ticking the score into their phone.

The rest of the date was just as much of an insane clash of personalities as normal. To be fair, Sans hadn't known your pollen allergy was that bad, so Papyrus felt he somewhat deserved the kick he got under the table for suggesting bringing flowers. He also had no idea what you had done to those poor chocolates, but from what you were saying, he was able to fathom a decent guess. Papyrus almost felt bad for you when Sans offered you a piece of your prank chocolates, but not really. You both needed a taste of your own medicine, and he was having far too much fun with your friend tallying score. He thought your melodramatic responses to the spicy candies was funny enough to even forgive Sans for swiping both his water and bottle of taco sauce.

(Your roommate was far kinder, even if they did chuckle all the way to the counter and back to get those milks to ease your suffering.)

The rest of the date had gone in much the same manner, ending when the two of you walked out, arm-in-arm, glaring at one another. Papyrus watched as you and Sans had a standoff by holding each other's door open for them until Sans walked over, picked you up, hauled you around to the other side of the car, and deposited you into your seat - with you yelling the whole time. As the waiter brought over his and your roommate's bill and another bottle of taco sauce, he nodded toward the shouting couple that had caused him so much bemusement.

"So," the waiter asked, "how many years have they been married?"

Papyrus found out that your roommate occasionally snorted while laughing that day.

On the way back, Papyrus enjoyed the flinches and groans you made whenever he announced his brother had scored another point. However, upon hearing that you were actually ahead, you let out a whoop of joy and did a small victory dance in your seat. Sans grimaced but caught Papyrus' eye in the rearview mirror, and Papyrus nodded. While you were busy rubbing it in Sans' face, Papyrus looked over to the nurse beside him and shared a wink. It had been their plan all along to try to get the two of you on "even ground", as it were, with hopes that they could make some rather obvious hints about how the two of you were a match for one another.

'If Sans doesn't like that pun, he can just bite me,' Papyrus texted the nurse. They snickered in response, fist bumping him in celebration of what was assuredly a victory. As he thought, Sans decided to "walk" you to your door, leaving you spluttering as he deposited you on the doorstep.

"Papyrus! Tell us the final score now!" Sans demanded.

With a nod from your roommate, Papyrus shifted the plastic straw in his mouth and said, "You both tied."

You made a squeak like a deflating whoopee cushion and started babbling about a recount. Sans smirked at you, looking every bit like the proud little skelly he was for tying with such a worthy opponent at such a challenge.

Then you had a last-ditch effort that threw a monkey wrench into all of Papyrus' plans:

"You mean a goodnight-"

"-kiss?" your roommate finished for him.

While you were busy distracting Sans with your teasing, Papyrus did a double take and looked over at your roommate. Oh, this was SO much better than what the two of them had thought out! Eagerly, Papyrus turned around right as he heard Sans take the bait and-

_Fucking. FINALLY!_

His brother had skipped straight from a simple kiss on the cheek to full-on face-to-face contact. Papyrus wasn't the most energetic monster, but he felt ready to dance a jig right there in the driveway. Instead, he looked to your roommate, who had pulled their fists down with a quiet "Yasssss!!!" and immediately started a series of victorious fist bumps with them. It looked like they wouldn't need that closet after all...

Papyrus watched you two stare like a Gyftrot in headlights at one another for a few moments before you noticed his little victory celebration. Sans noticed you had turned your attention away from him and saw where you were looking, bringing him back into reality so fast he went rigid. Papyrus couldn't help but laugh at his reaction to you realizing what had happened. Sans _saluted_ you. Of all things to do after a kiss, he SALUTED you! He spat out a "goodnight" before marching sharply back to the car, getting in, and driving off without even looking at him.

Sans made it to their driveway without a word. Papyrus watched, barely keeping the smile off his face, as he watched Sans remove the key from the ignition, choosing to sit and stare at the white vinyl that made up their garage door. After a moment, Sans spoke in an atypically small, almost deadpan voice:

"Papyrus?" 

"Yeah, Sans?"

"Did we just kiss?" 

Papyrus smirked. "Yeah, you did."

"Ah."

The dull _thunk!_ of Sans' forehead thumping against the car steering wheel was instantly drowned out by the blaring of the car horn. Papyrus couldn't stop laughing, which only got harder to stop when he saw Sans' magic begin trickling up from the sides of his face across the rest of his skull. Papyrus fished his phone out of his pocket, held it up, and did his best to record a video while he shook. 

A few moments later, he felt his phone vibrate and saw the recipient of the video was calling him.

With a grin, he swiped the alert across the screen and spoke into the phone.

"Well, Hell~o, Nurse!"


	2. PODFIC NOW AVAILABLE!

**Summary for the Chapter:**

> Podfic time!

**Notes for the Chapter:**

> A big thanks to Lovecakebacon and all of the lovely comments they've made about my podfics. 
> 
> I will be open to commissions soon for writing, podfics, and custom audio. In the meantime, don't forget to leave a comment or a suggestion over on my Tumblr: https://readwithdetermination.tumblr.com/

MEDIAFIRE: http://www.mediafire.com/file/yexbk2nmpdqw6r3/010_Matchmaker_Papyrus_and_his_Two_Tsunderes.mp3/file

YOUTUBE: 

**Author's Note:**

> Guess the reference!
> 
> Just remember: whenever you make a comment on a fanfic, an angel gets its wings!  
> ...No? That's not how the saying goes? Well, too bad, because it is now! XD


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